CN105949244A - Two green-light iridium phosphorescence complexes and synthesis method thereof - Google Patents
Two green-light iridium phosphorescence complexes and synthesis method thereof Download PDFInfo
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 30
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000001308 synthesis method Methods 0.000 title abstract 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003446 ligand Substances 0.000 claims abstract description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 238000003786 synthesis reaction Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 238000010189 synthetic method Methods 0.000 claims description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- TYPVHTOETJVYIV-UHFFFAOYSA-N 2,4-dichloropyridine Chemical compound ClC1=CC=NC(Cl)=C1 TYPVHTOETJVYIV-UHFFFAOYSA-N 0.000 claims description 3
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
- 239000012300 argon atmosphere Substances 0.000 claims description 2
- NAVNIBXODTVAEF-UHFFFAOYSA-N boric acid;1,3-difluorobenzene Chemical compound OB(O)O.FC1=CC=CC(F)=C1 NAVNIBXODTVAEF-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- -1 bis-{[2,4-bis(2,4-difluorophenyl) pyridine]} iridium chloride hydrate Chemical compound 0.000 abstract description 3
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 abstract 1
- PXVLHKKRTANMSX-UHFFFAOYSA-N 2,4-bis(2,4-difluorophenyl)pyridine Chemical compound FC1=C(C=CC(=C1)F)C1=NC=CC(=C1)C1=C(C=C(C=C1)F)F PXVLHKKRTANMSX-UHFFFAOYSA-N 0.000 abstract 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 abstract 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000000103 photoluminescence spectrum Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000002503 iridium Chemical class 0.000 description 3
- PSLMOSLVUSXMDQ-UHFFFAOYSA-N iridium;pentane-2,4-dione Chemical compound [Ir].CC(=O)CC(C)=O PSLMOSLVUSXMDQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 208000035126 Facies Diseases 0.000 description 1
- UVEMEJGROVJJAZ-UHFFFAOYSA-N [B].FC=1C=CC=C(C1)F Chemical compound [B].FC=1C=CC=C(C1)F UVEMEJGROVJJAZ-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
The invention relates to two green-light iridium phosphorescence complexes and a synthesis method thereof. The synthesis method comprises the following steps: taking 2,4-bis(2,4-difluorophenyl) pyridine as a main ligand; reacting with iridium chloride hydrate to obtain bis-{[2,4-bis(2,4-difluorophenyl) pyridine]} iridium chloride hydrate; and further reacting with (acetylacetone or 2,2,6,6-tetramethyl heptanedione) as an auxiliary ligand to obtain the two green-light iridium phosphorescence complexes with the following structure. Emission wavelengths of the two green-light iridium phosphorescence complexes are 515 nm and 526 nm, and the two green-light iridium phosphorescence complexes are green-light emitted iridium phosphorescence complexes.
Description
Technical field
The present invention relates to electromechanical phosphorescent material technology and synthetic method field, specifically one class fluorine replaces iridium phosphorescent complexes
With relevant synthetic method.
Background technology
Organic Light Emitting Diode (OLED), as efficient electro-optic conversion technology, becomes following novel display and lighting field
Important development direction.In many OLED material, luminescent material is the most key core material, its luminescent properties pair
The device performance of OLED has conclusive impact.Luminescent material has fluorescent material and the big class of phosphor material two, phosphor material
Luminous efficiency is 4 times of fluorescent material, and phosphor material is mainly the coordination compound of transition metal (Pt, Ir, Os, Cu etc.), wherein iridium
Phosphorescent complexes is the most efficient class electromechanical phosphorescent material, is widely used in OLED field.
Change the structure of main part and assistant ligand, all can regulate and control the maximum emission wavelength of iridium phosphorescent complexes and luminous effect
Rate, it is achieved the regulation and control to glow color.Green glow phosphor material OLED show and lighting field suffer from important application.Higher
One of efficiency and more long-life yellow light material focus being still current research.In consideration of it, the present invention designs has synthesized two kinds newly
The fluorine of the green emission of type replaces iridium phosphorescent complexes.
Summary of the invention
It is an object of the invention to provide a class novel fluorine substituted iridium phosphorescent complexes and synthetic method thereof.
Two all fluorine substituted iridium phosphorescent complexes that the present invention provides, they are two [2,4-bis-(2,4 difluorobenzene bases)
Pyridine] acetyl acetone iridium and two [2,4-bis-(2,4 difluorobenzene base) pyridines] (2,2,6,6-dipivaloylmethanes acid) close iridium,
They have following structural formula:
The invention provides a kind of method synthesizing above-mentioned iridium phosphorescent complexes, it comprises the following steps:
(1) synthesis of part
The synthesis of 2,4-bis-(2,4-3,5-dimethylphenyl) pyridine is to be former with 2,4-dichloropyridine and 2,4 difluorobenzene boric acid
Material, tetra-triphenylphosphine palladium be catalyst, oxolane and water be solvent, obtain part by suzuki coupling reaction.Concrete
Synthetic route and reaction condition are as follows:
(2) synthesis of iridium phosphorescent complexes
Under an argon atmosphere, with hydrated iridium trichloride as raw material, 2,4-bis-(2,4 difluorobenzene base) pyridine is that ring metal is joined
Body, ethylene glycol monoethyl ether and water (3:1) are solvent, back flow reaction 24 hours at 120 DEG C, cooling, filter, obtain after drying
Double-{ [2,4-bis-(2,4 difluorobenzene base) pyridine] } closes iridochloride, the assistant ligand of the amount of the most respectively with 2.5 times of materials
(acetylacetone,2,4-pentanedione or 2,2,6,6-dipivaloylmethanes), back flow reaction 4 hours at alkalescence condition and 135 DEG C, filters, dichloromethane
The quick post of crossing of alkane, then by dichloromethane and methanol mixed solvent recrystallization, obtains corresponding iridium phosphorescent complexes.Concrete
Synthetic route and reaction condition are as follows:
The present invention use elementary analysis, proton nmr spectra (1H NMR), mass spectrum, infrared spectrum confirm that part and iridium are joined
The structure of compound, obtains the optical physics parameter of iridium phosphorescent complexes by uv-vis spectra and photoluminescence spectra.
It is a feature of the present invention that and obtain two kinds of brand-new fluorine substituted iridium phosphorescent complexes and synthetic method thereof, can be rich
The research of rich OLED and the phosphor material of application.
Accompanying drawing explanation
The photoluminescence spectra of Fig. 1 bis-[2,4-bis-(2,4 difluorobenzene base) pyridine] acetyl acetone iridium；
Fig. 2 bis-[2,4-bis-(2,4 difluorobenzene base) pyridine] (acid of 2,2,6,6-dipivaloylmethane) closes the luminescence generated by light of iridium
Spectrum.
Detailed description of the invention
Embodiment one:
The synthesis of 2,4-bis-(2,4 difluorobenzene base) pyridine:
2 are added, 4-dichloropyridine (20.24g, 136.73mmol), 2,4 difluorobenzene boron in the three neck round bottom of 1L
Acid (23.75g, 150.4mmol), four (triphenyl phosphorus) palladium (2.75g, 2.38mmol) and natrium carbonicum calcinatum (68.0g,
641.32mmol), 200mL oxolane and 200mL secondary deionized water are then added, at N2Under protection, 70 DEG C of backflows are anti-
Answering 24h, remove solvent, add a large amount of deionized water after being cooled to room temperature, dichloromethane extracts three times, adds in the organic facies of extraction
Entering methanol, four (triphenyl phosphorus) palladium solid of precipitation reclaims, and filtrate uses anhydrous MgSO4It is dried.After being filtered to remove solvent, residue
Cross post and obtain pale yellow oil 30.3g, productivity 72.4%.
1. elementary analysis: theoretical value (%): C 67.33H 2.99N 4.62,
Measured value (%): C 67.31H 2.98N 4.63
2. nuclear magnetic resoance spectrum:1H-NMR(CDCl3,ppm):8.75(d,1H),8.03(td,1H)7.87(d,1H),7.49
(td,1H),7.40(dt,1H),6.97(m,4H).
3.ESI+-MS:m/z theoretical value: 303.25, measured value: 304
Embodiment two:
The synthesis of double-{ [2,4-bis-(2,4 difluorobenzene base) pyridine] } conjunction iridochloride:
Hydrated iridium trichloride (10.0g, 28.0mmol), 2,4-bis-(2,4-difluoros are added in 500ml three neck round bottom
Phenyl) pyridine (20.0g, 9.67mmol), add 240ml ethylene glycol monoethyl ether and 80ml secondary deionized water afterwards, at argon
Under protection, 120 DEG C of back flow reaction 24hrs.Being cooled to room temperature, filter, filter cake is respectively with ethanol and water washing, 60 DEG C of vacuum drying
24hrs, obtains double-{ [2,4-bis-(2,4 difluorobenzene base) pyridine] } and closes iridochloride 21.05g, productivity 83.7%.
Embodiment three:
The synthesis of two [2,4-bis-(2,4 difluorobenzene base) pyridine] acetyl acetone iridium:
In 500ml three neck round bottom, add double-{ [2,4-bis-(2,4 difluorobenzene base) pyridine] } close iridochloride
(10.03g, 5.6mmol), natrium carbonicum calcinatum (2.94g, 28mmol), acetylacetone,2,4-pentanedione (1.4g, 14mmol), add 200mL afterwards
Ethylene glycol monoethyl ether, takes out applying argon gas three times repeatedly, under argon shield, and 135 DEG C of back flow reaction 24h.It is cooled to room temperature, mixture
Pouring in a large amount of water, filter, filter cake dissolves with dichloromethane after drying, and crosses post, goes out after solvent, residue dichloromethane and
Target product 8.2g, productivity 81.5% is obtained after recrystallizing methanol.
1. elementary analysis: theoretical value (%): C 52.29H 2.59N 3.13,
Measured value (%): C 52.27H 2.60N 3.10
2. nuclear magnetic resoance spectrum: 1H-NMR (CDCl3): 8.48 (d, 2H), 8.41 (s, 2H), 7.65 (dt, 2H), 7.38 (dt,
2H),7.06(m,4H),6.36(m,2H),5.75(m,2H),5.29(s,1H),1.78(s,6H)
3.ESI-MS:m/z theoretical value: 895.82, measured value: 896
4. photoluminescence spectra: maximum emission wavelength is 515nm (Fig. 1), for green glow iridium phosphorescent complexes.
Embodiment four:
The synthesis of two [2,4-bis-(2,4 difluorobenzene base) pyridines] (acid of 2,2,6,6-dipivaloylmethane) conjunction iridium:
In 500ml three neck round bottom, add double-{ [2,4-bis-(2,4 difluorobenzene base) pyridine] } close iridochloride
(10.05g, 5.6mmol), natrium carbonicum calcinatum (2.94g, 28mmol), acetylacetone,2,4-pentanedione (1.4g, 14mmol), add 200mL afterwards
Ethylene glycol monoethyl ether, takes out applying argon gas three times repeatedly, under argon shield, and 135 DEG C of back flow reaction 24h.It is cooled to room temperature, mixture
Pouring in a large amount of water, filter, filter cake dissolves with dichloromethane after drying, and crosses post, goes out after solvent, residue dichloromethane and
Target product 8.7g, productivity 78.9% is obtained after recrystallizing methanol.
1. elementary analysis: theoretical value (%): C 55.15H 3.60N 2.86,
Measured value (%): C 55.14H 3.62N 2.84
2. nuclear magnetic resoance spectrum:1H-NMR(CDCl3,ppm):8.37(d,4H),7.63(dt,2H),7.30(dt,2H),7.08
(m,4H),6.37(m,2H),5.88(m,2H),5.30(s,1H),1.83(s,18H)
3.ESI-MS:m/z theoretical value: 979.98, measured value: 980
4. photoluminescence spectra: maximum emission wavelength is 526nm (Fig. 2), for green glow iridium phosphorescent complexes.
Claims (2)
1. two kinds of fluorine replace iridium phosphorescent complexes, it is characterised in that: the chemical constitution of described iridium phosphorescent complexes is as follows:
2. the synthetic method of two kinds of fluorine replacement iridium phosphorescent complexes as claimed in claim 1, it is characterised in that under including
Row step,
(1) synthesis of part:
The synthesis of 2,4-bis-(2,4-3,5-dimethylphenyl) pyridine be with 2,4-dichloropyridine and 2,4 difluorobenzene boric acid as raw material, four
Triphenylphosphine palladium be catalyst, oxolane and water be solvent, obtain part by suzuki coupling reaction.Concrete synthesis road
Line and reaction condition are as follows:
(2) synthesis of iridium phosphorescent complexes:
Under an argon atmosphere, with hydrated iridium trichloride as raw material, 2,4-bis-(2,4 difluorobenzene base) pyridine is cyclic metal complexes, second
2-ethoxyethanol and water (3:1) are solvent, back flow reaction 24 hours at 120 DEG C, cooling, filter, obtain after drying double-[2,
4-bis-(2,4 difluorobenzene base) pyridine] } close iridochloride, the assistant ligand (acetylacetone,2,4-pentanedione of the amount of the most respectively with 2.5 times of materials
Or 2,2,6,6-dipivaloylmethanes), back flow reaction 4 hours at alkalescence condition and 135 DEG C, filters, the quick mistake of dichloromethane
Post, then by dichloromethane and methanol mixed solvent recrystallization, obtains corresponding iridium phosphorescent complexes, concrete synthetic route
As follows with reaction condition:
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102484214A (en) * | 2009-08-24 | 2012-05-30 | E.I.内穆尔杜邦公司 | Organic light-emitting diode luminaires |
| CN103951707A (en) * | 2014-05-13 | 2014-07-30 | 深圳市华星光电技术有限公司 | Green ray iridium (III) complex as well as preparation method and application thereof |
| CN104628787A (en) * | 2015-01-22 | 2015-05-20 | 昆明贵金属研究所 | Green-emission iridium phosphors complex and preparation method thereof |
-
2016
- 2016-05-25 CN CN201610351281.4A patent/CN105949244A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102484214A (en) * | 2009-08-24 | 2012-05-30 | E.I.内穆尔杜邦公司 | Organic light-emitting diode luminaires |
| CN103951707A (en) * | 2014-05-13 | 2014-07-30 | 深圳市华星光电技术有限公司 | Green ray iridium (III) complex as well as preparation method and application thereof |
| CN104628787A (en) * | 2015-01-22 | 2015-05-20 | 昆明贵金属研究所 | Green-emission iridium phosphors complex and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| VYGINTAS JANKUS等，: "The role of exciplex states in phosphorescent OLEDs with poly(vinylcarbazole) (PVK) host", 《ORGANIC ELECTRONICS》 * |
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